Hydroxy sulfonic acids

Bisulfite Addition Compounds (see Hydroxy Sulfonic Acids)... 

Salts of sulfonic acids can be prepared by treatment of primary or secondary alkyl halides with sulfite ion,799 Even tertiary halides have been used, though the yields are low. Epoxides treated with bisulfite give 3-hydroxy sulfonic acids. ... 

Hydroxy Sulfonic Acids 0-41 Reaction between epoxides and bisulfite ion... 

Hydroxy olefins, see Olefinic alcohols a-Hydroxy sulfonic acids, conversion to a-amino cyanides, 606 preparation, 606... 

For preparation of orf/zo-halogenated phenols, S03H groups may be provisionally introduced at the positions that are not to be occupied by chlorine or bromine. The relevant hydroxy sulfonic acids are chlorinated or bromin-ated without being isolated, and the S03H groups are then hydrolysed off by steam-distilling the reaction mixture after it has been acidified with sulfuric acid. 

Preferably, however, the crude hydroxy sulfonic acids are halogenated in nitrobenzene-sulfuric acid. This affords yields of about 70% of 2,6-dichloro- or 2,6-dibromo-phenol, 72% of o-chlorophenol, or 46.5% of 0-bromophenol.450... 

A large number of oc-amino sulfonic acids have been prepared from the hydrogen sulfite adducts ( -hydroxy sulfonic acids) and ammonia or amines at or slightly above room temperature. 976They are very important intermediates in the Knoevenagel-Bucherer form of the Strecker amino acid synthesis (cf. page 877). In this synthesis the aldehyde-bisulfite compounds are converted by ammonia or amines into a-amino sulfonic acids and thence by alkali cyanide or hydrogen cyanide into oc-amino nitriles, which are then hydrolysed ... 

The reactions of enolized keto carboxylic esters with ammonia and amines are described on page 507, and those of a-amino alcohols, cyanohydrins, and a-hydroxy sulfonic acids on pages 516-520. 

Unless the carbonyl group is sterically strongly hindered by -substituents, as in aromatic ketones, the C-O double bond of most aldehydes and ketones readily adds hydrogen sulfite in an exothermic reaction, to give bisulfite compounds (geminal hydroxy sulfonic acids) these are easily reconverted into their components by acid or alkali. 

Chlorobutane gives 1- and 4-chloro-2-butanesulfonyl chloride and 4-chloro-l-butanesulfonyl chloride,204 hydrolysis of which affords the corresponding sulfonic acids 4-chloro-2- and -1-butanesulfonic acid lose hydrogen chloride when heated, passing into sultones205 (internal anhydrides of hydroxy sulfonic acids). 

Dye Intermediate, n.o.s. A cyclic compound, containing an amino, hydroxy, sulfonic acid, or quinone group or a combination of these groups used in the manufacture of dyes. ICAO A2... 

Amino-4-hydroxy sulfonic acid. See 2-Aminophenol-4-sulfonic acid... 

Amino-1-phenol-4-sulfonic acid. See2-Aminophenol-4-sulfonic acid 2-Aminophenol-4-sulfonic acid CAS 98-37-3 EINECS/ELINCS 202-662-8 Synonyms 3-Amino-4-hydroxy benzenesulfonic acid 3-Amino-4-hydroxy sulfonic acid 2-Amino-1-phenol-4-sulfonic acid o-Aminophenyl-p-sulfonic acid Empirical C6H7NO4S Formula C6H3OHNH2SO3H Properties Brn. rhombic cryst. or bik. powd. very... 

The first dissociation constant (Int. Crit. Tables VI, 260) of sulfurous acid is 1.7 X IQ- , whereas Stewart and Donnally found 3.7 X 10 for the a-hydroxy sulfonic acid of benzaldehyde at higher pH levels they established a second dissociation constant of 7 X 10 °. 

Sultones are the internal esters of hydroxy sulfonic acids and sulfur analogs of lactones. The biological activities of sultones are concerned with toxicological, skin sensitization, and antiviral properties [13]. In 2009, Majumdar developed a Pd(PPh3)4-catalyzed intramolecular C-H arylation reaction of benzenesulfonic acid 2-bromophenyl esters to afford polycyclic sultones, which are generally synthesized by elimination of the corresponding hydroxyl sulfonic acid derivatives, in up to 90% yield (Scheme 3.3, path a) [14]. TBAB was found to be critical in this reaction, and no reaction occurred in the absence of this additive. An electrophilic palladation mechanism was proposed for this transformation. 

Sultones are the internal esters of hydroxy sulfonic acids and are the sulfur analogs of lactones. Sultones are demanded scaffolds in medicinal chemistry research. Biological studies on sultones are mainly concerned with their toxicological, skin sensitization, and antiviral activities [20]. Sultones are synthetically useful heterocycles which can react with a variety of compounds to introduce the alkylsulfonic acid function and therefore used as sulfoalkylating agents [21]. There have been several new developments for the synthesis of sultones which have also been applied in the total synthesis of natural products. In recent years, the palladium-catalyzed direct arylation of several aromatics via a C-H bond activation using aryl halides has led to successes. An intramolecular version of this reaction has allowed the synthesis of several biaryls via the formation of five- to seven-membered rings. Thus, the sultones should be synthesized by C-H activation via two pathways (Scheme 4.14). 

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